US5969002A - Pigment preparations for inkjet printing - Google Patents

Pigment preparations for inkjet printing Download PDF

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Publication number
US5969002A
US5969002A US08/922,061 US92206197A US5969002A US 5969002 A US5969002 A US 5969002A US 92206197 A US92206197 A US 92206197A US 5969002 A US5969002 A US 5969002A
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weight
component
pigment
nco
groups
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Inventor
Johan Kijlstra
Stephan Kirchmeyer
Peter-Roger Nyssen
Dirk Pfutzenreuter
Christian Wamprecht
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Lanxess Deutschland GmbH
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium

Definitions

  • the invention relates to pigment preparations, a process for their preparation and their use as printing inks for inkjet printing.
  • Pigmented inks for inkjet printing are known per se.
  • Inkjet inks generally have pigment contents of 1 to 10% by weight, based on the ink.
  • Important application properties required of inkjet inks include, for example, a low viscosity, a high physical stability, good drying characteristics and also a suitable surface tension.
  • the water resistance of the resulting prints is important.
  • U.S. Pat. No. 4,597,794 discloses stabilizing the pigments in the printing inks with polymeric dispersants constructed of ionically hydrophilic and aromatically hydrophobic segments.
  • EP-A 518 225 and EP-A 556 649 describe acrylic block copolymers of the type AB, BAB and ABC for use as dispersants for pigments in printing inks.
  • E 0 to 20 equivalent %, based on the isocyanate groups of A), of formative components of the molecular weight range 32 to 3,000 g/mol which are at least difunctional for the purposes of the NCO addition reaction, with urethane and optionally urea formation while complying with an NCO number of 100 to 600, any excess NCO groups having reacted in simultaneous or subsequent secondary reactions down to a residual content of not more than 1.0% by weight.
  • Pigment preparations with component c) are specified in prior application DE-A 19 508 390, unpublished at the priority date of the present invention.
  • Component c) of the pigment preparations of the invention acts as a dispersant and comprises reaction products of polyisocyanates A) with monohydric alcohols B) and optionally further starting components C), D) and/or E), which reaction products have been prepared with urethane and optionally urea formation and have optionally been freed from any excess isocyanate groups by means of secondary reactions taking place simultaneously with and/or subsequent to the addition reaction leading to the urethane and optionally urea formation.
  • the content of free isocyanate groups is below 1% by weight. In general, no free isocyanate groups are detectable.
  • the component c) dispersant in the pigment preparations of the invention preferably contain 10 to 50 milliequivalents of ionic groups/100 g of component c), particularly preferably anionic groups in the form of carboxyl, sulphate, suiphonate, phosphate and phosphonate groups which are attached to the dispersant and which were converted, for example by means of alkali metal hydroxides or ethanolamine, di- or triethanolamine, into the corresponding salts.
  • Polyisocyanate component A) used for preparing component c) has an (average) NCO functionality of 1.7 to 6.0, preferably greater than 2.5, especially 3.0 to 6.0, and an NCO content of 5 to 65, preferably 7 to 30, % by weight.
  • Polyisocyanate components having an (average) NCO functionality of 1.7 to 2.5 are preferably raised, during the reaction with components B to E, to a functionality of greater than 2.5, by modification reactions.
  • Polyisocyanate component A) consists of at least one organic polyisocyanate.
  • Suitable polyisocyanates are unmodified polyisocyanates or modification products of conventional polyisocyanates, especially dilsocyanates, which conform to the stated specifications as regards NCO content and NCO functionality.
  • Unmodified polyisocyanates suitable for use as component A) or as part of component A) include for example the polyisocyanates of the diphenylmethane series, as produced alongside the corresponding diisocyanates in the phosgenation of aniline/formaldehyde condensates, or else conventional higher functional polyisocyanates such as, for example, 4,4',4"-triisocyanato-triphenylmethane.
  • polyisocyanates of component A consist of the aforementioned modification products of simple polyisocyanates.
  • Modification in this context is to be understood as meaning especially the preparation of biuret, allophanate and/or isocyanurate groups.
  • Diisocyanates to be used for preparing such derivatives include for example hexamethylene diisocyanate, cyclohexane 1,3- and 1,4-diisocyanate and also any mixtures of these isomers, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 2,4- and 2,6-hexahydro-toluylene diisocyanate and also any mixtures of these isomers, perhydro-2,4'- and/or -4,4'-diphenylmethane diisocyanate, 2,4- and 2,6-toluylene diisocyanate and also any mixtures of these isomers, diphenylmethane 2,4'- and/or 4,4'-diisocyanate and naphthylene 1,5-diisocyanate.
  • the modified diisocyanates For the preparation of the modified diisocyanates, particular preference is given to using the industrially important polyisocyanates, such as, for example, 2,4-diisocyanatotoluene, its technical grade mixtures with up to 35% by weight, based on mixture, of 2,6-diisocyanatotoluene, 4,4'-diisocyanatodiphenyl-methane, its technical grade mixtures with 2,4'- and 2,2'-diisocyanato-diphenylmethane, hexamethylene diisocyanate or mixtures of these diisocyanates.
  • the industrially important polyisocyanates such as, for example, 2,4-diisocyanatotoluene, its technical grade mixtures with up to 35% by weight, based on mixture, of 2,6-diisocyanatotoluene, 4,4'-diisocyanatodiphenyl-methane, its technical
  • the polyisocyanates of component A) are very particularly preferably the isocyanurate-functional modification products of 2,4-diiso-cyanatotoluene or its technical grade mixtures with up to 35% by weight, based on mixture, of 2,6-diisocyanatotoluene.
  • These particularly preferred isocyanurate-functional polyisocyanates generally have an NCO content of 7 to 30% by weight combined with an NCO functionality of 3 to 6.
  • the polyisocyanate component A) is frequently used in the form of a solution in an inert solvent such as, for example, butyl acetate.
  • a preferred embodiment comprises using a component A) comprising polyisocyanates having an average functionality of 1.7 to 2.5, the modification reactions, i.e. the formation of biuret, allophanate and/or isocyanurate groups, taking place parallel with or after the reaction of components B) to E).
  • modification reactions are known to the person skilled in the art and described for example in Houben-Weyl, Methoden der organischen Chemie, Volume E20, Makromolekulare Stoffe, ed. H. Bartl, J. Falbe, G. Thieme Verlag Stuttgart 1987, pages 1735, 1736 and 1739 to 1744.
  • the monohydric alcohol component B) consists of at least one monohydric alcohol having a molecular weight (computable from the hydroxyl group content) of 150 to 10,000, especially 150 to 5,000, preferably 500 to 3,000, g/mol, which has 40 to 99.5, preferably 70 to 99.5, % by weight, based on the total weight of the monohydric alcohol, of ethylene oxide units incorporated within a polyether chain.
  • a particularly suitable component B), or constituent of component B) comprises conventional alkoxylation products of monofunctional initiator molecules which, per molecule, have on average at least 3, preferably 7 to 250, alkylene oxide units which in turn comprise at least 40% by weight, preferably 70 to 100% by weight, of ethylene oxide units, based on the alkylene oxide unit.
  • Suitable initiator molecules for preparing the monohydric polyether alcohols include especially monofunctional alcohols, phenols or carboxylic acids.
  • the initiator molecules generally have 1 to 30, preferably 1 to 10, particularly preferably 1 to 4, carbon atoms.
  • Specific examples are alcohols such as methanol, ethanol, i-propanol, n-butanol, 1-pentanol, 1-hexanol, 1-octanol, oleyl alcohol or benzyl alcohol or phenols such as, for example, phenol, cresols, methylphenols, nonylphenols or dodecylphenols, or alkoxylatable acids such as, for example, acetic acid, butyric acid, capric acid, lauric acid, palmitic acid or stearic acid or else cyclohexanecarboxylic acid.
  • Preferred initiator molecules are monohydric alcohols of the above-exemplified type with 1 to 4 carbon atoms.
  • the conventional alkoxylation reaction is carried out using ethylene oxide or combinations of ethylene oxide with up to 60, preferably up to 30, % by weight, based on the total amount of alkylene oxide, of other alkylene oxides such as, in particular, propylene oxide. If, as well as ethylene oxide, other alkylene oxides are used, this can be done using appropriate alkylene oxide mixtures or else by successive addition of the alkylene oxides with block formation.
  • Component B) is used in an amount of 5 to 100, preferably 50 to 90, equivalent %, based on the isocyanate groups of component A).
  • the optional component C) consists of at least one other monofunctional compound, a compound which does not conform to the observations made under B) and which has an isocyanate-reactive group.
  • Suitable for this purpose are in particular the known monohydric alcohols such as, for example, methanol, ethanol, propanol, isopropanol, 1- and 2-butanol, isobutanol, 1-hexanol, 2-ethyl-1-hexanol, etc., also monohydric esteralcohols of the molecular weight range 94 to 350 such as, for example, methyl hydroxybutyrate, ethylene glycol monoacetate, propyl lactate or ethyl ⁇ -hydroxycaproate or monohydric alcohols of the molecular weight range 146 to 2,000 g/mol which are obtained by conventional addition of ⁇ -caprolactone to monohydric alcohols of the above-exemplified type.
  • Component C) is used in an amount of up to 20, preferably up to 10, equivalent %, based on the isocyanate groups of component A).
  • Component D) comprises organic compounds which, as well as at least one tert-amino group, have a group which is reactive towards isocyanate groups for the purposes of the isocyanate addition reaction, especially a hydroxyl or amino group. These compounds generally have a molecular weight of 80 to 250, especially 88 to 150, g/mol.
  • Examples of compounds suitable for use as component D), or as constituent of component D), are aminoalcohols such as N,N-diethylethanolamine, N,N-dimethylethanolamine, N,N-dimethylisopropanolamine, N,N-dimethyl-1,3-propanediamine, N,N-diethylethylenediamine, 2-dibutylaminoethanol, 3-(dimethylamino)-1-propanol, 1-methylpiperazine, 1-methyl-4-piperdinol, 2-morpholinoethanol, 2-piperidinoethanol, 2-piperazinoethanol, 2-piperazino-ethylamine, 3-morpholinopropylamine, N,N-dibutyltrimethylenediamine, 3-(diethylamino)-1-propanol, N-methyl-3-pyrrolidinol, 2-(hydroxymethyl)-N-methylpiperidine or polyamines having at least one tert-amino group and a primary or secondary amino group.
  • Preferred compounds for use as component D) or as constituent of component D) include 4-(2-hydroxyethyl)pyridine, 2-hydroxyethylmorpholine, N,N-dimethyl-l1,3-propanediamine, N,N-diethyl-1,4-butanediamine and N,N-dimethylaminoethanol and N,N-dimethylaminopropylamine.
  • Component D) is used in an amount of from 0 to 50, preferably 10 to 50, equivalent %, based on the isocyanate group of component A).
  • Component D) is preferably used in such an amount that the addition products which are essential to the invention contain 0 to 200, and especially 0 to 100, milliequivalents of tert-amino groups per 100 g of solids.
  • the optional component E) comprises organic compounds of the molecular weight range 32 to 3,000, preferably 118 to 2,000, g/mol which have two groups reactive towards isocyanate groups, these groups being two alcoholic hydroxyl groups, in particular.
  • Examples are in particular polyester- or polyether-diols of the conventional kind within the stated molecular weight range.
  • Component E if used at all, is used in the preparation of the addition compounds which are essential to the invention in an amount of up to 20, preferably up to 10, equivalent %, based on the isocyanate groups of component A). It is particularly preferable not to use component E).
  • Preferred pigment preparations of the invention are characterized in that the polyisocyanate addition product of component c) has been prepared with an NCO number of 100 to 130 by reaction of
  • pigment preparations of the invention are characterized in that the polyisocyanate addition product of component c) has been prepared with an NCO number of 131 to 600 by reaction of
  • pigment preparations of the invention which are characterized in that the polyisocyanate addition product of component c) contains 10 to 50 milliequivalents of ionic groups per 100 g of component c).
  • the essential addition products can be prepared from the exemplified starting materials A) to E) according to various methods.
  • the reaction takes place in the melt at temperatures of 20 to 250° C., preferably 60 to 140° C.
  • a possible procedure comprises for example reacting the isocyanate component A) with a mixture of component B) and optionally C), D) and/or E), or else first preparing an NCO prepolymer from component A) and a portion of reactants B) to E) and then reacting it in a 2nd stage with the rest of the reactants with isocyanate-reactive groups.
  • NCO excess is reduced by secondary reactions to a residual level of not more than 1.0% by weight, preferably 0.5% by weight, particularly preferably 0% by weight.
  • secondary reactions is the formation of allophanate groups, biuret groups, uretdione groups or isocyanurate groups by corresponding addition or addition-polymerization reactions of the excess NCO groups.
  • Such reactions are frequently catalysed by the tertiary nitrogen atoms present and brought about by heating to 60 to 250° C. for 0.1 to 24 hours.
  • Preferred secondary reactions are addition-polymerization reactions leading to the formation of uretdione groups and/or isocyanurate groups.
  • a particularly preferred secondary reaction is the addition polymerization of the remaining NCO groups to form isocyanurate structures which form under catalysis of tertiary nitrogen atoms optionally appearing from component D) or by addition of further trimerization catalysts.
  • Suitable trimerization catalysts for trimerizing the excess NCO groups in the process of the invention include all compounds hitherto used in the preparation of isocyanurate polyisocyanates. Specific examples are oxides, for example lithium oxide or bis[tributyltin] oxide; alkoxides such as, for example, sodium methoxide or potassium tert-butoxide; phenoxides, hydrides, such as, for example, sodium boranate; hydroxides, for example quaternary ammonium, phosphonium, arsonium, stibonium hydroxides or potassium hydroxide/crown ethers; amines, for example triethylamine, benzyldimethylamine, Mannich bases of phenols, pyrazines or 1-(2-hydroxyethyl)aziridine; amides, for example acrylamides and carbamnidic esters; aminimides, for example N,N-dimethyl-N-(2-hydroxypropyl)laurinimide
  • Good trimerization catalysts also include a number of combinations of substances which by themselves have little if any activity, for example tetramethylammonium iodide/(phenoxymethyl)oxirane, 1,4-diaza-bicyclo-[2.2.2]octane/(phenoxymethyl)oxirane or cyclohexyldimethylamine/tetramethylammonium 2-ethylhexanoate.
  • tetramethylammonium iodide/(phenoxymethyl)oxirane 1,4-diaza-bicyclo-[2.2.2]octane/(phenoxymethyl)oxirane or cyclohexyldimethylamine/tetramethylammonium 2-ethylhexanoate.
  • the reaction apart from the minimal solvents optionally used for dissolving component A), is advantageously performable in the melt, it is also possible to use inert solvents, for example to reduce the viscosity.
  • suitable solvents are dimethylformamide, N-methylpyrrolidone, dimethylacetamide, acetone, 2-butanone, ethyl acetate, butyl acetate, methoxypropyl acetate, toluene or mixtures of such solvents.
  • the solvents are removed in the course of the reaction or subsequently, for example by distillation.
  • catalysts for the isocyanate addition reaction are triethylamine, N,N-dimethylbenzylamine or tin compounds such as, for example, tin(II) octoate or dibutyltin dilaurate.
  • Pigments for the purposes of the present invention are water-insoluble colorants.
  • the pigments used preferably have an average particle size of 0.005 to 5 ⁇ m, especially 0.005 to 1 ⁇ m.
  • the maximum single particle size is particularly preferably below 0.5 ⁇ m, which ensures blockage-free flow through the fine nozzle holes of the printing head (generally 10 to 50 ⁇ m) and adequate physical stabilization of the pigment preparations throughout the use and storage time by the dispersant described as component c).
  • a very fine division coupled with a narrow particle diameter distribution is advantageous.
  • the pigments can in principle be used in the form of their dry powders, granules or water-moist press cakes.
  • Suitable pigments include not only inorganic and organic colour pigments but also carbon black, of which a large number are known for example from the Colour Index, 2nd edition.
  • Carbon blacks to be mentioned in particular are acidic to alkaline carbon blacks from the group of the furnace or gas blacks and also chemically or physically modified or aftertreated carbon blacks.
  • Suitable inorganic pigments include for example zinc sulphides, ultramarine, iron oxides, cobalt blue and also chromium oxide pigments.
  • Suitable pigments in the wider sense also include pigments in the form of finely particulate oxides such as silicon dioxide, titanium dioxide, nickel oxides, chromium antimony titanium dioxides, aluminium oxide and also finely particulate metals such as copper, iron or aluminium.
  • Suitable organic colour pigments include for example those of the azo, disazo, polyazo, anthraquinone, thioindigo series, also other polycyclic pigments such as, for example, from the phthalocyanine, quinacridone, dioxazine, isoindolinone, naphthalenetetracarboxylic acid and perylene and perylenetetracarboxylic acid series, also those of the perinone, indigoid, thioindigoid or diketopyrrolopyrrole series, and also metal complex pigments of azo, azomethine or methine dyes or laked dyes such as calcium, magnesium, aluminium lakes of sulpho- and/or carboxyl-containing dyes.
  • the pigment preparations of the invention can contain mixtures of various organic pigments or organic and inorganic pigments.
  • the pigment preparations of the invention can of course also contain further additives as well as components a), b) and c).
  • Suitable optional further additives include additives customary for inkjet printing inks.
  • organic solvents can be present as further component d).
  • water-soluble organic solvents Preference is given to those which have a solubility of greater than 0.5 g/100 g of water.
  • Suitable organic solvents include:
  • aliphatic C 1 -C 4 -alcohols such as methanol, ethanol, isopropanol, n-propanol, n-butanol, isobutanol or tert-butanol
  • aliphatic ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or diacetone alcohol
  • polyols such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, trimethylolpropane, polyethylene glycol having an average molecular weight of 100 to 4000, preferably 400 to 1500, g/mol or glycerol
  • monohydroxyethers preferably monohydroxyakl ethers, particularly preferably mono-C 1 -C 4 -alkyl glycol ethers such as ethylene glycol monoalkyl, monomethyl, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether, diethylene glyco
  • the amount of organic solvent is preferably 1 to 40, in particular 2 to 20, % by weight, based on the pigment preparations.
  • the amount of water and organic solvent is preferably 20 to 99% by weight, preferably 30 to 97% by weight, based on the pigment preparations.
  • the pigment preparations may further contain agents for setting the viscosity of the ink such as, for example, polyvinyl alcohol, polyvinylpyrrolidone, methylcellulose and other agents known to the person skilled in the art, provided they do not adversely affect the stability of the printing ink, the printing characteristics and the drying characteristics on paper.
  • agents for setting the viscosity of the ink such as, for example, polyvinyl alcohol, polyvinylpyrrolidone, methylcellulose and other agents known to the person skilled in the art, provided they do not adversely affect the stability of the printing ink, the printing characteristics and the drying characteristics on paper.
  • the printing ink can contain 0 to 15% by weight, preferably 0.5 to 10% by weight, based on the ink, of a surface-active agent.
  • a surface-active agent can be used in principle, for example, to regulate the surface tension of the ink, also to prevent drop formation or leakage at the jet exit surface of the printing head and to adjust the wetting and drying characteristics of the ink on various types of substrates (papers).
  • Such surface-active agents are known to the person skilled in the art in the form of commercially available products. The surface-active agent chosen must not impair the stability of the pigment preparation or the printing head materials used.
  • the pigment preparation of the invention can contain further ionic as well as nonionic auxiliaries. If the polyisocyanate addition product (component c) contains ionic groups, these auxiliaries should preferably be nonionic or of identical ionogeneity.
  • the pigment preparations can additionally contain preservatives, light stabilizers, further surfactants and optionally also pH regulators.
  • pH regulators are NaOH, ammonia or aminomethylprepanol, N,N-dimethylaminomethanol.
  • preservatives are methyl- and chloromethyl-isothiazolin-3-one, benzisothiazolin-3-one or mixtures thereof.
  • UV absorbers examples are UV absorbers.
  • pigment preparations comprising
  • aliphatic C 1 -C 4 -alcohols such as methanol, ethanol, isopropanol, n-propanol, n-butanol, isobutanol or tert-butanol
  • aliphatic ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or diacetone alcohol
  • polyols such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, trimethylolpropane, polyethylene glycol having an average molecular weight of 100 to 4000, preferably 400 to 1500, g/mol or glycerol
  • monohydroxyethers preferably monohydroxyalkyl ethers, particularly preferably mono-C 1 -C 4 -alkyl glycol ethers such as ethylene glycol monoalkyl, monomethyl, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether, diethylene
  • the invention further relates to the production of the novel pigment preparations for inkjet printing, which is characterized in that at least one pigment and the dispersant of component c) and optionally further additives are homogenized and wet-comminuted.
  • the pigment in powder form or in the form of the water-moist press cake, is beaten together with a portion of the dispersant and water, preferably deionized water, for example by means of a stirred vat, dissolver or similar machines, optionally after precomminution, to form a homogeneous millbase suspension.
  • the dispersant and water preferably deionized water
  • the millbase suspension can additionally contain portions of low boiling solvents (boiling point ⁇ 150° C.) which can be carried off, through evaporation, in the course of the subsequent fine milling. However, it can also contain portions of higher boiling solvents or further additives such as, for example, thiodiglycol or, as described above, for example milling auxiliaries, defoaming or wetting agents.
  • the wet comminution comprises not only the precomminution but also the fine milling.
  • the pigment concentration of the suspension is preferably above the concentration desired for the finished pigment preparation or printing ink.
  • the desired pigment end concentration is preferably set following the wet comminution.
  • the precomminution is followed by milling to the desired particle fine division of from 0.001 to 5 ⁇ m, preferably 0.005 to 1 ⁇ m. Suitable apparatus for this milling includes for example kneaders, roller mills, kneading screws, ball mills, rotor-stator mills, dissolvers, corundum disc mills, vibratory mills and especially high speed, continuously or discontinuously charged stirred ball mills with grinding media having a diameter of 0.1 to 2 mm.
  • the grinding media can be of glass, ceramic or metal, for example steel.
  • the milling temperature is preferably within the range from 0 to 250° C., but generally at room temperature, especially below the turbidity point of the dispersants used as component c) and any surface-active agents used.
  • the milling can take place wholly or partly in a high pressure homogenizer or in a so-called jet disperser (known from prior, unpublished application DE-A 19 536 845), whereby the level of grinding media detritus in the suspension or the release of soluble substances from the grinding media (e.g. ions from glass media) can be reduced to a minimum or completely avoided.
  • a so-called jet disperser known from prior, unpublished application DE-A 19 536 845
  • the resulting pigment preparation is conventionally mixed into water, optionally with the remaining dispersant quantities and optionally further additives, and homogenized and also adjusted to the desired pigment end concentration or colour strength of the preparation or printing ink.
  • a portion of the dispersant can additionally be added if desired, for example to avoid a reagglomeration of fine pigment particles in the dilution.
  • An example of the process for removing dispersant present in solution is centrifugation of the suspension and subsequent decanting off of the supernatant.
  • additives such as, for example, polyurethane or acrylic polymers can be added to further improve the water resistance, if necessary.
  • additives such as, for example, polyurethane or acrylic polymers can be added to further improve the water resistance, if necessary.
  • These can be not only of the water-soluble but also of the water-emulsifiable type, or be soluble in one of the components present in d).
  • the mixing and homogenizing of the pigment preparations is effected using a jet disperser or high pressure homogenizer to prevent the formation of foam and avoid possible reagglomeration.
  • the standardizing of the desired pigment preparations also involves standardization to the desired viscosity, colour strength, hue, density and surface tension of the ink.
  • the inks are fine-filtered if necessary, for example by means of 1 to 5 ⁇ m membrane or glass filters.
  • the physical ink properties are adjusted for use in conventional inkjet printers, for which the surface tension should be between 20 and 70 mN/m and the viscosity should be less than 20 mPa.s, preferably 0.5 to 10 mPa.s.
  • the pigment preparations of the invention When used as printing inks in inkjet printing they provide prints having excellent lightfastness and additionally have the following advantages: excellent dispersing and storage stability over a wide temperature range; good printability; high water and migration resistance of the prints on various substrates, for example on lignin-free paper, average paper quality, sized and coated paper, polymeric films, transparencies for overhead projection; they are suitable for multicolour printing, even if used together with dye inks or other pigmented inks.
  • the resulting aqueous pigment concentrate was adjusted to a pigment concentration of 20% by weight with
  • the pigment preparation possesses excellent flowability and perfect suspension stability in 3 months' storage at room temperature and 50° C. Aqueous dilutions of these preparations down to a pigment concentration of 2% are likewise stable.
  • composition can be found in Table 1.
  • Example 4 is repeated using the 40% strength aqueous solution of the polyisocyanate addition product of Example 2, affording a black pigment preparation having likewise excellent stability and flow properties.
  • composition can be found in Table 1.
  • the millbase suspension was diluted to a pigment concentration of 5% with deionized water and centrifugated on a laboratory centrifuge (from Sigma) at a speed of 20,000/1 minute for a period of 8 hours.
  • the substantially clear supernatant was decanted off.
  • the resulting concentrate was adjusted with deionized water to a solids content of 20% and preservatived as described in Example 4.
  • the pigment preparation has adequate flowability and perfect suspension stability.
  • the composition can be found in Table 1.
  • Example 6 was repeated without the step of dilution and centrifugation and using the 40% strength aqueous solution of the polyisocyanate addition product of Example 3, affording a magenta pigment preparation having likewise excellent stability and flow properties.
  • the composition can be found in Table 1.
  • the pigment preparations of Examples 4 to 7 were diluted for use as inkjet printing inks to a pigment concentration of 4% by weight in each case using deionized water and organic solvents.
  • the composition of the pigment preparations to be used as printing inks were each chosen so that the viscosity of the printing inks is within the range from 3 to 5 mPas.
  • the preparation was carried out starting from the pigment preparations of Examples 4 to 7 by mixing and stirring the necessary amount of water and also other additives such as organic solvent in a glass vessel. This was followed by an ultrasonication for 1 minute and addition of preservative and optionally pH adjustment by means of dilute NaOH.
  • the composition of the pigment preparations used as printing inks is revealed in Table 2.
  • pigment preparations were filtered through a 1.2 ⁇ m filter before printing to remove any grinding media detritus and oversize from the suspension.
  • the printing inks of Examples 8 to 11 possess excellent suspension stability after storage at room temperature and 50° C. for a period of 3 months. No flocculation or reaggregation of the pigment particles was observed, and the viscosity of the printing inks is unchanged.
  • the printing inks were satisfactorily printable on commercially available inkjet printers. They produced bright prints of high colour strength, good contrast and high lightfastness.
  • the water resistance was tested by preparing prints on a commercially available inkjet printer from Hewlett Packard (HP Deskjet® 1600C) using the black cartridge in the form of a bar chart on normal paper (AGFA 701® from Agfa-Gaevert).
  • the water resistance was determined by means of a test in which a drop of water was made to run over the print at different time intervals following the preparation of the print and measuring the amount of colorant entrained by the water as a measure of the water resistance.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
US08/922,061 1996-09-09 1997-09-02 Pigment preparations for inkjet printing Expired - Fee Related US5969002A (en)

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DE19636382 1996-09-09
DE19636382A DE19636382A1 (de) 1996-09-09 1996-09-09 Pigmentpräparationen für den Ink-Jet-Druck

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EP (1) EP0827973B1 (de)
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US6136890A (en) * 1998-02-17 2000-10-24 3M Innovative Properties Company Ink jet ink containing polyurethane dispersant
US6166105A (en) * 1998-10-13 2000-12-26 Eastman Kodak Company Process for making an ink jet ink
US6468340B1 (en) 2000-10-30 2002-10-22 Hewlett-Packard Company Laked dye solubilization with complexing agent
WO2003046038A1 (en) * 2001-11-24 2003-06-05 Avecia Limited Aqueous urethane dispersants
US6680355B1 (en) 1998-09-18 2004-01-20 Basf Aktiengesellschaft Dispersant
US20040242726A1 (en) * 2002-05-16 2004-12-02 Minoru Waki Pigment dispersion and ink composition for ink-jet
US20040251331A1 (en) * 2002-09-05 2004-12-16 Archibald Vere Orland Method of producing fine solid particles and dispersions
EP1557448A1 (de) 2004-01-26 2005-07-27 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Nassmahlverfahren unter Verwendung von Mikrokugeln
US20050247235A1 (en) * 2004-05-06 2005-11-10 Agfa-Gevaert N.V. Multi-density ink-jet ink set for ink-jet printing
US20050250869A1 (en) * 2004-05-06 2005-11-10 Agfa-Gevaert N.V. Radiation-curable ink-jet printing
WO2005090447A3 (de) * 2004-03-15 2006-05-04 Basf Ag Verwendung von n-ethyl-2-pyrrolidon
US20060092254A1 (en) * 2004-10-29 2006-05-04 Agfa-Gevaert Printing of radiation curable inks into a radiation curable liquid layer
US20060132566A1 (en) * 2004-12-16 2006-06-22 Agfa-Gevaert Dotsize control fluid for radiation curable ink-jet printing process
US20060170745A1 (en) * 2004-12-21 2006-08-03 Agfa-Gevaert Ink-jet ink set for producing images with large colour gamut and high stability
US20070148460A1 (en) * 2003-12-18 2007-06-28 Basf Aktiengesellschaft Pigments sheathed with polyaddition products, method for their produciton and use thereof
US20080139735A1 (en) * 2005-02-08 2008-06-12 Basf Aktiengesellschaft Solid Pigment Preparations Containing Water-Soluble Surface-Active Polyurethane-Base Additives
US20080168922A1 (en) * 2004-11-25 2008-07-17 Tokai Carbon Co., Ltd. Carbon Black Aqueous Dispersion and Method of Producing the Same
US20080182080A1 (en) * 2005-02-24 2008-07-31 Basf Aktiengesellschaft Pigments That Are At Least Partially Sheathed In Radiation-Curable Polyurethane, Their Production And Use
WO2009076381A1 (en) * 2007-12-10 2009-06-18 E. I. Du Pont De Nemours And Company Urea-terminated polyurethane dispersants
US20090320912A1 (en) * 2006-06-10 2009-12-31 Konarka Technologies, Inc. Component with a Structured Layer on a Carrier Substrate
US20110021699A1 (en) * 2008-02-22 2011-01-27 Byk-Chemie Gmbh Wetting agents and dispersants, their preparation and use
EP2235113A4 (de) * 2007-12-21 2011-08-24 Upm Kymmene Oyj Verfahren zur herstellung eines organischen pigments
US8362104B2 (en) 2003-03-24 2013-01-29 Chimigraf Iberica, Sl Method for the production of a digital printing ink and product thus produced
CN102939345A (zh) * 2010-05-31 2013-02-20 东海炭素株式会社 聚氨酯树脂附着颜料，颜料分散组合物以及喷墨墨组合物
CN103805002A (zh) * 2012-11-02 2014-05-21 大金工业株式会社 涂料组合物、太阳能电池组件背板以及太阳能电池组件
US9068092B2 (en) 2011-07-07 2015-06-30 Fujifilm Imaging Colorants Limited Process for preparing polymers, polymers, dispersions, inks and uses
US9434808B2 (en) 2011-07-07 2016-09-06 Fujifilm Imaging Colorants Limited Process for preparing polymers, polymers, dispersions, inks and uses
US9441121B2 (en) 2011-10-05 2016-09-13 Fujifilm Imaging Colorants Limited Dispersions, process for preparing dispersions, inks and uses
US9777175B2 (en) 2013-03-05 2017-10-03 Cabot Corporation Aqueous pigment dispersions
US10208215B2 (en) 2014-02-06 2019-02-19 Oce-Technologies B.V. Ink composition, pinning agent and print method

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JP3897268B2 (ja) * 1998-06-16 2007-03-22 サカタインクス株式会社 インクジェット記録用インク
DE50005383D1 (de) * 1999-06-21 2004-04-01 Surface Specialties Austria Wasserverdünnbare Harze, Verfahren zu ihrer Herstellung und ihre Verwendung
DE10039837C2 (de) * 2000-08-16 2003-03-20 Byk Chemie Gmbh Verfahren zur Herstellung einer lagerstabilen, rheologisch wirksamen Harnstoffurethan-Lösung mit breiter Verträglichkeit
JP5055653B2 (ja) * 2000-08-18 2012-10-24 リコープリンティングシステムズ株式会社 インクジェット用インク組成物を用いた記録方法
US7074850B2 (en) 2001-09-26 2006-07-11 Basf Aktiengesellschaft Cross-linkable polyurethane block copolymers and their use in dispersion binding agent systems
EP1671805B1 (de) 2004-12-16 2009-03-11 Agfa Graphics N.V. Verfahren zum Tintenstrahldrucken mit strahlenhärtbarer Tinte bei welchem eine Flüssigkeit zur Kontrolle der Punktgrösse verwendet wird
US7465343B2 (en) 2005-05-13 2008-12-16 Hewlett-Packard Development Company, L.P. Inkjet ink for use on polymeric substrate
PL1911814T5 (pl) 2006-10-11 2023-12-11 Agfa Nv Sposoby sporządzania zestawów utwardzalnych pigmentowanych tuszów do druku atramentowego
JP7160532B2 (ja) 2015-03-20 2022-10-25 ブルー キューブ アイピー エルエルシー 硬化性組成物

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Cited By (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6136890A (en) * 1998-02-17 2000-10-24 3M Innovative Properties Company Ink jet ink containing polyurethane dispersant
US6680355B1 (en) 1998-09-18 2004-01-20 Basf Aktiengesellschaft Dispersant
US6166105A (en) * 1998-10-13 2000-12-26 Eastman Kodak Company Process for making an ink jet ink
US6468340B1 (en) 2000-10-30 2002-10-22 Hewlett-Packard Company Laked dye solubilization with complexing agent
WO2003046038A1 (en) * 2001-11-24 2003-06-05 Avecia Limited Aqueous urethane dispersants
US8664331B2 (en) 2001-11-24 2014-03-04 The Lubrizol Corporation Aqueous urethane dispersants
US20040260013A1 (en) * 2001-11-24 2004-12-23 Richards Stuart Nicholas Aqueous urethane dispersants
EP1505128A4 (de) * 2002-05-16 2005-11-16 Seiko Epson Corp Pigmentdispersion und tintenzusammensetzung für tintenstrahldruck
US20040242726A1 (en) * 2002-05-16 2004-12-02 Minoru Waki Pigment dispersion and ink composition for ink-jet
US7858676B2 (en) 2002-05-16 2010-12-28 Seiko Epson Corporation Pigment dispersion and ink composition for ink jet printing
US20080108746A1 (en) * 2002-05-16 2008-05-08 Seiko Epson Corporation Pigment dispersion and ink composition for ink jet printing
US6896212B2 (en) 2002-09-05 2005-05-24 Rohm And Haas Company Method of producing fine solid particles and dispersions
US20040251331A1 (en) * 2002-09-05 2004-12-16 Archibald Vere Orland Method of producing fine solid particles and dispersions
US8362104B2 (en) 2003-03-24 2013-01-29 Chimigraf Iberica, Sl Method for the production of a digital printing ink and product thus produced
US20070148460A1 (en) * 2003-12-18 2007-06-28 Basf Aktiengesellschaft Pigments sheathed with polyaddition products, method for their produciton and use thereof
EP1557448A1 (de) 2004-01-26 2005-07-27 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Nassmahlverfahren unter Verwendung von Mikrokugeln
EP1557448B1 (de) * 2004-01-26 2011-06-08 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Nassmahlverfahren unter Verwendung von Mikrokugeln
US7553365B2 (en) 2004-01-26 2009-06-30 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Water-based pigment dispersions, inkjet recording inks, and color filters
US20050164101A1 (en) * 2004-01-26 2005-07-28 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Water-based pigment dispersions, inkjet recording inks, and color filters
WO2005090447A3 (de) * 2004-03-15 2006-05-04 Basf Ag Verwendung von n-ethyl-2-pyrrolidon
US20050250869A1 (en) * 2004-05-06 2005-11-10 Agfa-Gevaert N.V. Radiation-curable ink-jet printing
US8083338B2 (en) 2004-05-06 2011-12-27 Agfa Graphics N.V. Radiation-curable ink-jet printing
US20050247235A1 (en) * 2004-05-06 2005-11-10 Agfa-Gevaert N.V. Multi-density ink-jet ink set for ink-jet printing
US7520601B2 (en) 2004-10-29 2009-04-21 Agfa Graphics, N.V. Printing of radiation curable inks into a radiation curable liquid layer
US20060092254A1 (en) * 2004-10-29 2006-05-04 Agfa-Gevaert Printing of radiation curable inks into a radiation curable liquid layer
US20080168922A1 (en) * 2004-11-25 2008-07-17 Tokai Carbon Co., Ltd. Carbon Black Aqueous Dispersion and Method of Producing the Same
TWI386463B (zh) * 2004-11-25 2013-02-21 東海炭素股份有限公司 Carbon black water dispersion and a method for producing the same
US7575314B2 (en) 2004-12-16 2009-08-18 Agfa Graphics, N.V. Dotsize control fluid for radiation curable ink-jet printing process
US20060132566A1 (en) * 2004-12-16 2006-06-22 Agfa-Gevaert Dotsize control fluid for radiation curable ink-jet printing process
US20060170745A1 (en) * 2004-12-21 2006-08-03 Agfa-Gevaert Ink-jet ink set for producing images with large colour gamut and high stability
US20080139735A1 (en) * 2005-02-08 2008-06-12 Basf Aktiengesellschaft Solid Pigment Preparations Containing Water-Soluble Surface-Active Polyurethane-Base Additives
US9045644B2 (en) * 2005-02-08 2015-06-02 Basf Aktiengesellschaft Solid pigment preparations containing water-soluble surface-active polyurethane-base additives
US20080182080A1 (en) * 2005-02-24 2008-07-31 Basf Aktiengesellschaft Pigments That Are At Least Partially Sheathed In Radiation-Curable Polyurethane, Their Production And Use
US20090320912A1 (en) * 2006-06-10 2009-12-31 Konarka Technologies, Inc. Component with a Structured Layer on a Carrier Substrate
WO2009076381A1 (en) * 2007-12-10 2009-06-18 E. I. Du Pont De Nemours And Company Urea-terminated polyurethane dispersants
US9410010B2 (en) 2007-12-10 2016-08-09 E I Du Pont De Nemours And Company Urea-terminated polyurethane dispersants
EP2235113A4 (de) * 2007-12-21 2011-08-24 Upm Kymmene Oyj Verfahren zur herstellung eines organischen pigments
US9085654B2 (en) 2008-02-22 2015-07-21 Byk-Chemie Gmbh Wetting agents and dispersants, their preparation and use
US20110021699A1 (en) * 2008-02-22 2011-01-27 Byk-Chemie Gmbh Wetting agents and dispersants, their preparation and use
US20130165584A1 (en) * 2010-05-31 2013-06-27 Tokai Carbon Co., Ltd. Polyurethane resin adhesion pigment, pigment dispersion composition and inkjet ink composition
CN102939345A (zh) * 2010-05-31 2013-02-20 东海炭素株式会社 聚氨酯树脂附着颜料，颜料分散组合物以及喷墨墨组合物
US9045583B2 (en) * 2010-05-31 2015-06-02 Tokai Carbon Co., Ltd. Polyurethane resin adhesion pigment, pigment dispersion composition and inkjet ink composition
US9434808B2 (en) 2011-07-07 2016-09-06 Fujifilm Imaging Colorants Limited Process for preparing polymers, polymers, dispersions, inks and uses
US9068092B2 (en) 2011-07-07 2015-06-30 Fujifilm Imaging Colorants Limited Process for preparing polymers, polymers, dispersions, inks and uses
US9441121B2 (en) 2011-10-05 2016-09-13 Fujifilm Imaging Colorants Limited Dispersions, process for preparing dispersions, inks and uses
CN103805002A (zh) * 2012-11-02 2014-05-21 大金工业株式会社 涂料组合物、太阳能电池组件背板以及太阳能电池组件
US9777175B2 (en) 2013-03-05 2017-10-03 Cabot Corporation Aqueous pigment dispersions
US10208215B2 (en) 2014-02-06 2019-02-19 Oce-Technologies B.V. Ink composition, pinning agent and print method

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JPH10183044A (ja) 1998-07-07
JP4101330B2 (ja) 2008-06-18
EP0827973B1 (de) 2004-12-22
DE19636382A1 (de) 1998-03-12
EP0827973A1 (de) 1998-03-11
DE59712126D1 (de) 2005-01-27

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